ethyl N-(3-chlorophenylmethyl)pipecolinate | 247104-95-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: ethyl N-(3-chlorophenylmethyl)pipecolinate
• 英文别名: Ethyl n-(3chlorophenylmethyl)pipecolinate；ethyl 1-[(3-chlorophenyl)methyl]piperidine-2-carboxylate
• CAS: 247104-95-6
• 化学式: C₁₅H₂₀ClNO₂
• mdl: MFCD22376912
• 分子量: 281.782
• InChiKey: OKWZVESJICBOHU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.533
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl N-(3-chlorophenylmethyl)pipecolinate 在 盐酸 、 PPA 、 四氯化钛 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 8.0h， 生成 8-chloro-N-methyl-1,2,3,4,6,11a-hexahydrobenzo[b]quinolizin-11-imine
  参考文献：
  名称：

  Syntheses of benzoquinolizidine and benzoindolizidine derivatives as anti-amnesic agents

  摘要：

  Tacrine, one of the drugs available for Alzheimer's disease based on the cholinergic approach, suffers from considerable toxicity. Many analogues of tacrine have been prepared which retain the pharmacologically rich aminopyridine or aminoquinoline motifs. The current research was undertaken to produce an acetylcholinesterase inhibitor by employing 11-aminobenzoquinolizidines (4) and 10-aminobenzoindolizidines (5) as templates. Thus, we aimed to achieve three goals relative to tacrine: eliminate the pyridine and quinoline moieties and render the molecule less flat. Overall, the compounds we prepared were poorer inhibitors of acetylcholinesterase compared to tacrine. The single exception was compound 6f which exhibited an effect comparable to that of tacrine, but only at a dose of the order of 10(-3) M. However, despite the poor acetylcholinesterase inhibition by 6b, this compound proved to be an effective anti-amnesic agent at 45 mg/kg dose. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00078-4
• 作为产物：
  描述：

  2-哌啶甲酸乙酯盐酸盐 、 间氯氯苄 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 以2.79 g的产率得到ethyl N-(3-chlorophenylmethyl)pipecolinate
  参考文献：
  名称：

  Syntheses of benzoquinolizidine and benzoindolizidine derivatives as anti-amnesic agents

  摘要：

  Tacrine, one of the drugs available for Alzheimer's disease based on the cholinergic approach, suffers from considerable toxicity. Many analogues of tacrine have been prepared which retain the pharmacologically rich aminopyridine or aminoquinoline motifs. The current research was undertaken to produce an acetylcholinesterase inhibitor by employing 11-aminobenzoquinolizidines (4) and 10-aminobenzoindolizidines (5) as templates. Thus, we aimed to achieve three goals relative to tacrine: eliminate the pyridine and quinoline moieties and render the molecule less flat. Overall, the compounds we prepared were poorer inhibitors of acetylcholinesterase compared to tacrine. The single exception was compound 6f which exhibited an effect comparable to that of tacrine, but only at a dose of the order of 10(-3) M. However, despite the poor acetylcholinesterase inhibition by 6b, this compound proved to be an effective anti-amnesic agent at 45 mg/kg dose. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00078-4

文献信息

• Benzoquinolizidine and benzoindolizidine derivatives and therapeutic uses thereof
  申请人：American Biogenetic Sciences, Inc.

  公开号：US06436954B1

  公开（公告）日：2002-08-20

  Benzo[b]quinolizidine and benzo[f]indolizidine derivatives are provided which are useful for the treatment of Alzheimer's disease, senile dementia or other conditions characterized by memory loss. Pharmaceutical compositions containing these compounds, and methods for their use, are also provided.

  本文提供了苯并[b]喹啉和苯并[f]吲哚啉衍生物，这些衍生物可用于治疗阿尔茨海默病、老年性痴呆或其他以记忆丧失为特征的疾病。本文还提供了含有这些化合物的药物组合物以及它们的使用方法。
• BENZOQUINOLIZIDINE AND BENZOINDOLIZIDINE DERIVATIVES AND THERAPEUTIC USES THEREOF
  申请人：AMERICAN BIOGENETIC SCIENCES, INC.

  公开号：EP1098650A1

  公开（公告）日：2001-05-16
• US6436954B1
  申请人：——

  公开号：US6436954B1

  公开（公告）日：2002-08-20
• [EN] BENZOQUINOLIZIDINE AND BENZOINDOLIZIDINE DERIVATIVES AND THERAPEUTIC USES THEREOF<br/>[FR] DERIVES DE BENZOQUINOLIZIDINE ET DE BENZO-INDOLIZIDINE ET LEUR USAGE THERAPEUTIQUE
  申请人：AMERICAN BIOGENETIC SCIENCES

  公开号：WO2000004905A1

  公开（公告）日：2000-02-03

  Benzo[b]quinolizidine and benzo[f]indolizidine derivatives are provided which are useful for the treatment of Alzheimer's disease, senile dementia, or other conditions characterized by memory loss. Pharmaceutical compositions containing these compounds, and methods for their use, are also provided.